1990 Fiscal Year Final Research Report Summary
Study on Stereoselective Synthesis of Biologically Active Substances Utilizing Organometallic Compounds
| Project/Area Number |
01470087
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
YAMAMOTO Keiji Department of Chemical Engineering, Tokyo Institute of Technology Professor, 工学部, 教授 (80025999)
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| Co-Investigator(Kenkyū-buntansha) |
MIYAZAWA Masahiro Same as above, Research Associate, 工学部, 助手 (70209899)
TAKAHASHI Takashi Same as above, Associate Professor, 工学部, 助教授 (80110724)
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| Project Period (FY) |
1989 – 1990
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| Keywords | Zincate complex / Prostaglandin / Three-Component-Coupling / Kinetic Resolution / Conjugate Addition / pi-Allylpalladium / 1, 3-Chirality Transfer / Optically Active |
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| Research Abstract |
A serious sideーreaction, proton transfer, which is usually observed in the conjugate addition to cyclopentenone (1) followed by alkylation of the resulting metal enolate (2), as depicted in Scheme 1, is eliminated by utilizing newly developed zincate (7) (Scheme 2). In the case of the conjugate addition of an excess <plus-minus>-cis omegaーside chain, an efficient kinetic resolution takes place, giving Stereochemically homogeneous 12 (Scheme 3
Also, a novel cyclization is developed by an intramolecular olefin insertion to piーallylic palladium complexes, and applied to the stereoselective synthesis of prostanoid frameworks with 1, 3-chirality transfer starting from 3-oxoー8, 9-dihydroxytetradecaー1, 6-diene derivatives.
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